WO2010001977A1 - Assaisonnement contenant un peptide - Google Patents

Assaisonnement contenant un peptide Download PDF

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Publication number
WO2010001977A1
WO2010001977A1 PCT/JP2009/062154 JP2009062154W WO2010001977A1 WO 2010001977 A1 WO2010001977 A1 WO 2010001977A1 JP 2009062154 W JP2009062154 W JP 2009062154W WO 2010001977 A1 WO2010001977 A1 WO 2010001977A1
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WO
WIPO (PCT)
Prior art keywords
fermented seasoning
activity
peptide
soy sauce
fermented
Prior art date
Application number
PCT/JP2009/062154
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English (en)
Japanese (ja)
Inventor
仲原　丈晴
理一郎 内田
花田　洋一
良知 遠藤
茂紀 谷沢
仁美 青田
精一 原
Original Assignee
キッコーマン株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by キッコーマン株式会社 filed Critical キッコーマン株式会社
Priority to KR1020107029561A priority Critical patent/KR101679870B1/ko
Priority to EP09773555.9A priority patent/EP2298085B1/fr
Priority to CN200980125965.0A priority patent/CN102083328B/zh
Priority to US13/001,931 priority patent/US8691302B2/en
Publication of WO2010001977A1 publication Critical patent/WO2010001977A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/24—Synthetic spices, flavouring agents or condiments prepared by fermentation
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/50—Soya sauce

Definitions

  • the present invention relates to a fermented seasoning having a good flavor and having little peptide bitterness despite being rich in peptides.
  • a method for producing a peptide As a method for producing a peptide, a method of chemically synthesizing or a method of hydrolyzing a protein-containing material with a protease agent is widely used as a well-known method. In the former case, however, a chemical is used. It is unsuitable for ingestion, and in the latter case, there are problems that the production cost is high and that the ingestion is not easy due to the strong bitterness of the peptide.
  • soy sauce is a seasoning that has been used since ancient times, but a rich umami is brought about by the decomposition of enzymes produced by koji molds in soybeans and wheat.
  • This umami occurs when proteases act on the raw protein to solubilize as peptides, and peptidases act on these peptides to decompose them into amino acids such as glutamic acid.
  • soy sauce technology development for many years has focused on degrading proteins and peptides to amino acids as much as possible to enhance the taste.
  • soy sauce In the brewing of soy sauce, it is considered that the peptide remains in the soy sauce if it is not decomposed by the peptidase after being released by the protease. Therefore, although it is expected to have various beneficial physiological activities as described above, it is extremely difficult to specifically control the peptidase activity in the normal charging process, so such soy sauce or fermented seasoning The fee has never been invented.
  • the problem to be solved by the present invention is to provide a fermented seasoning that does not have a bitter taste peculiar to a peptide and is easy to be taken orally despite containing a lot of peptides having useful physiological activity.
  • LAP-I activity in moromi mash is 1.0 U / ml or less
  • leucine aminopeptidase-II activity is 0.5 U / ml
  • the fermented seasoning obtained by controlling to less than ml has a sufficient nitrogen utilization rate, but surprisingly contains much more peptide than ordinary soy sauce, and does not feel the bitterness peculiar to peptides, and is mellow. It discovered that it had abundant umami
  • the present invention 1) Bacilli culture, or a mixture of Aspergillus oryzae culture and plant-derived protein raw material, charged with salt water, and within 10 days after charging, the leucine aminopeptidase-I activity in the moromi soup is 1.0 U / ml And a fermented seasoning obtained by controlling leucine aminopeptidase-II activity to 0.5 U / ml or less, 2) The fermented seasoning according to 1) above, wherein the soluble total nitrogen is 1.2% or more and the soluble peptide is 40 mg / ml or more, 3) The fermented seasoning according to 1) or 2) above, wherein the soluble total nitrogen is 1.2% or more and the amination ratio to the soluble total nitrogen is 55% or less, 4) The fermented seasoning according to any one of 1) to 3) above, wherein the soluble total nitrogen is 1.2% or more and the free amino group concentration per 1% of the soluble total nitrogen is 0.35 mol / L or less.
  • a fermented seasoning is provided.
  • a fermented seasoning which does not have a bitter taste peculiar to peptides but can be easily taken orally despite containing a lot of useful physiologically active peptides.
  • FIG. 2 is a diagram showing an HPLC chromatogram of composition 1.
  • FIG. It is a figure which shows the HPLC chromatogram of dark mouth soy sauce. It is a figure which shows the change of the systolic blood pressure when the direction whose blood pressure is high ingested the fermented seasoning of this invention.
  • the fermented seasoning of the present invention is prepared by adding salt water to a koji mold culture or a mixture of koji mold culture and plant-derived protein raw material, and leucine aminopeptidase-I activity in moromi mash juice within 10 days after charging Is controlled to 1.0 U / ml or less and leucine aminopeptidase-II activity to 0.5 U / ml or less.
  • a soy sauce koji widely used in soy sauce brewing can be used.
  • a koji mold is inoculated into a solid medium containing soybeans, wheat, etc. It can be obtained by culturing at 45 ° C. for 12 to 240 hours.
  • liquid culture koji used for the production of fermented seasonings can also be used.
  • koji molds are inoculated into a liquid medium containing 1 to 5% soybean, wheat, wheat bran, etc. It can be obtained by culturing at 45 ° C. for 24 to 120 hours.
  • any material can be used as long as the object of the present invention can be achieved, but in order to give a suitable flavor as a seasoning, soybeans, defatted soybeans, purified soybean proteins, Wheat, wheat gluten, rice, or purified rice protein should be used.
  • These raw materials can be used after being subjected to protein denaturation treatment as they are or after being crushed and pulverized.
  • protein denaturation treatment pressure steaming and puffing treatment, which are widely used in industry, are preferable.
  • the charging conditions are as follows: Aspergillus oryzae culture and plant-derived protein material mixed at a ratio of 5:95 to 100: 0, preferably 10:90 to 80:20, and 30 to 500% by weight, preferably Add 100-300% saline.
  • the concentration of the saline solution may be adjusted to 0.1 to 20%, preferably 6 to 18%, as the salt concentration of the moromi soup.
  • this mixture is put in a container capable of temperature control and fermented at 25 to 60 ° C., preferably 30 to 55 ° C., for 6 to 720 hours, preferably 12 to 240 hours. During this time, moromi may be appropriately stirred with a stirring blade or compressed air.
  • the desired fermented seasoning can be obtained by controlling the LAP-I activity in the moromi soup to 1.0 U / ml or less and the LAP-II activity to 0.5 U / ml or less within 10 days after charging. it can.
  • the fermented seasoning is in the form of soy sauce moromi, but a liquid fermented seasoning containing a soluble peptide can also be obtained by removing solids as necessary.
  • the solid content can be removed by wrapping the moromi in a filter cloth made of synthetic fiber such as nylon and pressurizing, or by putting the moromi in a filter cloth stretched between the filter plate and the compression plate, and using compressed air.
  • a known method such as a filter press method in which pressure is applied can be used.
  • a yeast such as Tigosaccharomyces
  • 10 4 pieces / ml to 10 8 pieces / ml, preferably 10 5 to 10 7 pieces / ml of yeast are added to moromi, and 20 to 35 ° C., preferably 25 to 30 ° C., for 3 days.
  • it is preferably fermented for 5 to 10 days.
  • stirring and aeration are appropriately performed.
  • the amount of peptides hardly decreases.
  • the fermented seasoning is remarkably different from the conventionally known peptide-containing compositions, and hardly has a bitter taste, and is mild and rich with mild and rich umami and richness. It has a good aroma and can be ingested deliciously as a seasoning.
  • the fermented seasoning has a preferred flavor, it can be added to soy sauce to make soy sauce or processed soy sauce, or mixed with various raw materials to prepare soy sauce, sauce, pants, sauce, dressing, soup, side dish It is also suitable for processing into beverages and supplements.
  • the peptide can be concentrated or separated and purified from the fermented seasoning.
  • Examples of the method include vacuum concentration, ultrafiltration, dialysis, various chromatographies and the like. These are generally widely used methods.
  • Soy sauce cake was obtained by adding spores of Aspergillus soya to a solid medium containing equal amounts of heat-denatured soybean and wheat and smelting at 25 to 40 ° C. for 72 hours. Next, 14 kg of heat-denatured soybean, 2 kg of soy sauce cake, 16 L of water and 3 kg of sodium chloride were mixed and stirred at 45 ° C. and 100 rpm. After 10 days, moromi was obtained in which the LAP-I activity in the moromi mash was reduced to 1.0 U / ml or less and the LAP-II activity was reduced to 0.5 U / ml or less.
  • yeast Tigosaccharomyces rouxii was mixed at a rate of 1.5 ⁇ 10 6 pieces / ml and allowed to stand at 25 ° C. for 7 days.
  • an insoluble solid was removed from the moromi using a hydraulic press to obtain a clarified liquid.
  • enzyme inactivation and sterilization were performed by heating at 117 ° C. for 5 seconds using an HS sterilizer (manufactured by Nisaka Seisakusho), and after standing at 50 ° C. for 3 days, only the supernatant containing no sputum component was obtained. 20 L was collected (Composition 1; the present invention fermented seasoning).
  • the fermented seasoning was prepared by the same method using 3.2 kg of soybeans and 12.8 kg of soy sauce cake. (Composition 2; fermented seasoning of the present invention). Furthermore, a fermented seasoning was prepared in the same manner using 16 kg of soy sauce koji without adding soybean at the time of preparation (Composition 3; the fermented seasoning of the present invention).
  • LAP-I activity was measured by the method described in Japanese Patent No. 3727780 using L-leucine-p-nitroanilide as a substrate.
  • the LAP-II activity is described in Japanese Patent No. 3727780 by using moromi soup on a PD-10 column (GE Healthcare Buy Science) to remove free amino acids and using L-leucyl-glycyl-glycine as a substrate. It measured by the method of.
  • Acid carboxypeptidase (ACP) activity was measured according to a conventional method using an acid carboxypeptidase activity measurement kit (manufactured by Kikkoman Corp.) after removing the free amino acid from the moromi soup on a PD-10 column.
  • Dipeptidyl peptidase IV (DPP-IV) activity is determined according to Agnes Doumas et al. , Applied and Environmental Microbiology, 1998, vol. 64, no. 12, p. It was measured by the method described in 4809-4815 (Table 1). Even when ACP and DPP-IV were charged at 45 ° C. for 10 days, the activity did not change to 15 ° C., but the activity of LAP decreased at 45 ° C.
  • composition 3 fermented seasoning of the present invention.
  • compositions 1, 2 various enzyme activities in moromi decreased further
  • compositions 1, 2 the present invention fermented seasoning
  • the same fermented seasoning as the composition 3 was prepared using koji of different production lots, a case having a higher LAP activity than the present invention was also observed (Comparative Example 1).
  • Soluble total nitrogen (TN) was measured according to a conventional method using a Keltec autosampler system 1035 (manufactured by Actac). The amount of peptide was heated at 110 ° C. for 24 hours in the presence of 6N hydrochloric acid, and then analyzed for all amino acids using an amino acid analyzer L-8500 (manufactured by Hitachi, Ltd.). Asked. The amination rate is the ratio of the total amino acid concentration to TN. In addition, 6.25 which is a general nitrogen coefficient of soybean protein was used for calculation of TN.
  • the free amino group concentration was determined by reacting with an equal amount of OPA reagent (manufactured by Agilent Technologies), measuring fluorescence intensity at Ex: 350 nm, Em: 450 nm, and using a calibration curve prepared with glycine at known concentrations.
  • the amounts of Gly-Tyr and Ser-Tyr were determined by an addition calibration curve method using an LC-MS / MS system 2695-QuatroMicro API (manufactured by Waters).
  • Compositions 1, 2, and 3 (invented fermented seasoning) with reduced LAP activity have a higher amount of peptide, lower amination rate, and lower free amino group concentration per TN of 1% than concentrated soy sauce. (Table 2).
  • Comparative Example 1 prepared in the same manner as Composition 3 using cocoons of different production lots has a low peptide amount, a high amination rate, and a high free amino acid concentration per TN 1%. Therefore, in order to obtain the fermented seasoning containing a high peptide content of the present invention, it is essential to control the LAP-I activity to 1.0 U / ml or less and the LAP-II activity to 0.5 U / ml or less. It can be said that this has not been known in the past.
  • HPLC High-performance liquid chromatography
  • Composition 1 the present invention fermented seasoning
  • Puresil C18 column 4.6 ⁇ 250 mm, manufactured by Waters
  • Detection was at an absorbance of 220 nm. It is generally known that most of the peaks observed under these analysis conditions are derived from peptides. 1 and FIG.
  • composition 1 shows a wide variety of peptides, and the amount thereof is significantly higher than that of ordinary concentrated soy sauce.
  • the large peaks (indicated by ⁇ ) of 15 minutes, 18 minutes, and 23 minutes that are also observed in concentrated soy sauce are not peptides but amino acids Tyr, Phe, and Trp, respectively. It was also confirmed that the other amino acids were hardly retained in this column and eluted in 5 minutes or less.
  • a fermentation seasoning was prepared in the same manner using Alcalase 2.4L-FG (manufactured by Novozymes), which is a food protease agent, instead of soy sauce cake (Comparative Example 2). Sensory evaluation was performed using composition 1 (present invention fermented seasoning) and Comparative Example 2. The panel consisted of 8 persons, and “bitterness strength” and “taste taste” were evaluated by a paired comparison method. From the results in Table 3, it can be seen that the fermented seasoning of the present invention has a good taste with little bitterness despite containing a large amount of peptide. Although many methods for producing peptides using protease agents have been disclosed so far, the present invention is considered superior to the prior art in terms of taste.
  • Subjects were allowed to ingest the test food or control food once a day for 12 weeks by using one bag (8 ml) for cooking at any time (standard daily intake of soy sauce 8 ml at home) Per minute, containing 430 ⁇ g of Gly-Tyr and 250 ⁇ g of Ser-Tyr).
  • a gradual antihypertensive effect was observed over time by ingesting the test food of the present invention (FIG. 3), and the systolic blood pressure significantly decreased after 4 weeks of ingestion compared with the value before ingestion. Indicated.
  • systolic blood pressure significantly decreased after 8 weeks after ingestion.
  • the fermented seasoning of the present invention has a significant antihypertensive action by the peptide as compared with the reduced salt soy sauce, and contains Gly-Tyr of 40 ⁇ g / ml or more and Ser-Tyr of 20 ⁇ g / ml or more. It became clear that the effect was remarkable.
  • the fermented seasoning obtained by the present invention contains a large amount of peptide, it has no bitterness peculiar to peptides and is easy to take orally, so it can be expected to exert useful physiological activity and contribute to people's health. .

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Biotechnology (AREA)
  • Soy Sauces And Products Related Thereto (AREA)
  • Seasonings (AREA)

Abstract

L'invention concerne un assaisonnement fermenté qui contient une grande quantité d'un peptide ayant une activité physiologique utile, mais ne présentant pas l'amertume caractéristique du peptide, et qui peut par conséquent être facilement administré oralement. L'assaisonnement fermenté est obtenu en ajoutant une solution aqueuse de chlorure de sodium à une culture de champignon koji, qui a été, en option, mélangée avec un matériau protéique d'origine végétale, en réduisant le mélange obtenu en purée et, dans les 10 jours qui suivent cette opération, en régulant l'activité de la leucine aminopeptidase I du moût (moromi) à 1,0 U/ml ou moins, et l'activité de la leucine aminopeptidase II à 0,5 U/ml ou moins.
PCT/JP2009/062154 2008-07-02 2009-07-02 Assaisonnement contenant un peptide WO2010001977A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
KR1020107029561A KR101679870B1 (ko) 2008-07-02 2009-07-02 펩티드 함유 조미료
EP09773555.9A EP2298085B1 (fr) 2008-07-02 2009-07-02 Assaisonnement contenant un peptide
CN200980125965.0A CN102083328B (zh) 2008-07-02 2009-07-02 含肽的调味料
US13/001,931 US8691302B2 (en) 2008-07-02 2009-07-02 Peptide-containing seasoning

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2008172871 2008-07-02
JP2008-172871 2008-07-02
JP2009-153239 2009-06-29
JP2009153239A JP5626748B2 (ja) 2008-07-02 2009-06-29 ペプチド含有調味料

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WO2010001977A1 true WO2010001977A1 (fr) 2010-01-07

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US (1) US8691302B2 (fr)
EP (1) EP2298085B1 (fr)
JP (1) JP5626748B2 (fr)
KR (1) KR101679870B1 (fr)
CN (1) CN102083328B (fr)
WO (1) WO2010001977A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102933100A (zh) * 2010-02-23 2013-02-13 格里菲斯实验室国际股份有限公司 包含天然代谢物的用于肉和海鲜的腌泡汁

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2517577B1 (fr) * 2009-12-25 2018-09-12 Kikkoman Corporation Procédé pour produire sauce au soja ayant des effets hypotensifs
CN102630923A (zh) * 2012-04-19 2012-08-15 华南理工大学 一种酱油的制备方法
GB201520499D0 (en) * 2015-11-20 2016-01-06 Medical Res Council Technology Compounds
JP7008452B2 (ja) 2017-09-25 2022-01-25 花王株式会社 高吸収型経口チロシン製剤

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JPH08173093A (ja) 1994-12-27 1996-07-09 Kao Corp 食品用組成物、苦味低減化法、及び栄養食品
JPH08252075A (ja) * 1995-03-16 1996-10-01 Ajinomoto Co Inc 酵素分解型調味料
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JP2006075064A (ja) 2004-09-09 2006-03-23 Sanei Gen Ffi Inc ペプチド含有飲料
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JP2008172871A (ja) 2007-01-09 2008-07-24 Toyota Motor Corp 固定子モールド成形方法、及び固定子構造
JP2009153239A (ja) 2007-12-18 2009-07-09 Sumitomo Wiring Syst Ltd 電気接続箱

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JP2006075064A (ja) 2004-09-09 2006-03-23 Sanei Gen Ffi Inc ペプチド含有飲料
JP2007097465A (ja) 2005-10-04 2007-04-19 Calpis Co Ltd 苦味、渋味が低減されたペプチド含有飲食品およびその製造方法
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See also references of EP2298085A4 *
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102933100A (zh) * 2010-02-23 2013-02-13 格里菲斯实验室国际股份有限公司 包含天然代谢物的用于肉和海鲜的腌泡汁

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EP2298085A4 (fr) 2011-11-30
JP5626748B2 (ja) 2014-11-19
JP2010029183A (ja) 2010-02-12
EP2298085A1 (fr) 2011-03-23
KR20110036009A (ko) 2011-04-06
CN102083328A (zh) 2011-06-01
CN102083328B (zh) 2017-08-25
US20110104334A1 (en) 2011-05-05
KR101679870B1 (ko) 2016-11-25
EP2298085B1 (fr) 2015-09-09
US8691302B2 (en) 2014-04-08

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